Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry

Alotamide is a cyclic depsipetide isolated from a marine cyanobacterium and possesses a unique activation of calcium influx in murine cerebrocortical neurons (EC<sub>50</sub> 4.18 µM). Due to its limited source, the three stereocenters (C19, C28, and C30) in its polyketide fragm...

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Main Authors:	Hao-yun Shi, Yang Xie, Pei Hu, Zi-qiong Guo, Yi-hong Lu, Yu Gao, Cheng-gang Huang
Format:	Article
Language:	English
Published:	MDPI AG 2018-10-01
Series:	Marine Drugs
Subjects:	alotamide asymmetric synthesis relative structural determination
Online Access:	https://www.mdpi.com/1660-3397/16/11/414

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spelling	doaj-119680ee32114d72bba9dab96cb64e4f2020-11-25T02:11:07ZengMDPI AGMarine Drugs1660-33972018-10-01161141410.3390/md16110414md16110414Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative StereochemistryHao-yun Shi0Yang Xie1Pei Hu2Zi-qiong Guo3Yi-hong Lu4Yu Gao5Cheng-gang Huang6Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, ChinaShanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, ChinaShanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, ChinaShanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, ChinaShanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, ChinaShanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, ChinaShanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, ChinaAlotamide is a cyclic depsipetide isolated from a marine cyanobacterium and possesses a unique activation of calcium influx in murine cerebrocortical neurons (EC<sub>50</sub> 4.18 µM). Due to its limited source, the three stereocenters (C19, C28, and C30) in its polyketide fragment remain undetermined. In this study, the first asymmetric synthesis of its polyketide fragment was achieved. Four relative possible diastereomers were constructed with a boron-mediated enantioselective aldol reaction and Julia⁻Kocienski olefination as the key steps. Comparison of <sup>13</sup>C NMR spectra revealed the relative structure of fragment C15⁻C32 of alotamide.https://www.mdpi.com/1660-3397/16/11/414alotamideasymmetric synthesisrelative structural determination
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Hao-yun Shi Yang Xie Pei Hu Zi-qiong Guo Yi-hong Lu Yu Gao Cheng-gang Huang
spellingShingle	Hao-yun Shi Yang Xie Pei Hu Zi-qiong Guo Yi-hong Lu Yu Gao Cheng-gang Huang Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry Marine Drugs alotamide asymmetric synthesis relative structural determination
author_facet	Hao-yun Shi Yang Xie Pei Hu Zi-qiong Guo Yi-hong Lu Yu Gao Cheng-gang Huang
author_sort	Hao-yun Shi
title	Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry
title_short	Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry
title_full	Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry
title_fullStr	Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry
title_full_unstemmed	Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry
title_sort	asymmetric synthesis of the c15–c32 fragment of alotamide and determination of the relative stereochemistry
publisher	MDPI AG
series	Marine Drugs
issn	1660-3397
publishDate	2018-10-01
description	Alotamide is a cyclic depsipetide isolated from a marine cyanobacterium and possesses a unique activation of calcium influx in murine cerebrocortical neurons (EC<sub>50</sub> 4.18 µM). Due to its limited source, the three stereocenters (C19, C28, and C30) in its polyketide fragment remain undetermined. In this study, the first asymmetric synthesis of its polyketide fragment was achieved. Four relative possible diastereomers were constructed with a boron-mediated enantioselective aldol reaction and Julia⁻Kocienski olefination as the key steps. Comparison of <sup>13</sup>C NMR spectra revealed the relative structure of fragment C15⁻C32 of alotamide.
topic	alotamide asymmetric synthesis relative structural determination
url	https://www.mdpi.com/1660-3397/16/11/414
work_keys_str_mv	AT haoyunshi asymmetricsynthesisofthec15c32fragmentofalotamideanddeterminationoftherelativestereochemistry AT yangxie asymmetricsynthesisofthec15c32fragmentofalotamideanddeterminationoftherelativestereochemistry AT peihu asymmetricsynthesisofthec15c32fragmentofalotamideanddeterminationoftherelativestereochemistry AT ziqiongguo asymmetricsynthesisofthec15c32fragmentofalotamideanddeterminationoftherelativestereochemistry AT yihonglu asymmetricsynthesisofthec15c32fragmentofalotamideanddeterminationoftherelativestereochemistry AT yugao asymmetricsynthesisofthec15c32fragmentofalotamideanddeterminationoftherelativestereochemistry AT chengganghuang asymmetricsynthesisofthec15c32fragmentofalotamideanddeterminationoftherelativestereochemistry
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Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the Relative Stereochemistry

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